Which of the following bases would favorably deprotonate a hydroxyl group?
(d) Et₃N

Verified step by step guidance

Understand the concept of deprotonation: Deprotonation is the removal of a proton (H⁺) from a molecule, which in this case is a hydroxyl group (OH). The ability of a base to deprotonate a hydroxyl group depends on its strength and the stability of the resulting anion.

Consider the acidity of the hydroxyl group: Hydroxyl groups are generally weak acids, meaning they do not easily lose their proton. Therefore, a strong base is typically required to deprotonate them.

Evaluate the base in question: Triethylamine (Et₃N) is a tertiary amine. Amines are generally considered weak bases compared to other stronger bases like alkoxides or hydroxides.

Compare the base strength: To determine if Et₃N can deprotonate a hydroxyl group, compare its basicity to that of other bases. Strong bases like sodium hydroxide (NaOH) or potassium tert-butoxide (KOtBu) are more likely to deprotonate hydroxyl groups.

Consider steric effects: Triethylamine is a bulky base due to its three ethyl groups, which can hinder its ability to approach and deprotonate the hydroxyl group effectively. This steric hindrance can reduce its effectiveness as a base in deprotonation reactions.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above.

Was this helpful?

Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Acid-Base Chemistry

Acid-base chemistry involves the transfer of protons (H⁺) between molecules. A base is a substance that can accept a proton, while an acid is a substance that can donate a proton. Understanding the strength of acids and bases, often measured by pKa values, is crucial for predicting the outcome of deprotonation reactions.

pKa and Deprotonation

The pKa value of a compound indicates its acidity; lower pKa values correspond to stronger acids. Deprotonation occurs when a base removes a proton from an acid. For a base to deprotonate a hydroxyl group effectively, it must be strong enough to overcome the acid's pKa, meaning the base should have a higher affinity for the proton than the hydroxyl group does.

Steric and Electronic Effects

Steric and electronic effects influence a base's ability to deprotonate an acid. Steric hindrance can impede a base's approach to the proton, while electronic effects, such as the presence of electron-donating or withdrawing groups, can stabilize or destabilize the base or the conjugate acid. In the case of triethylamine (Et₃N), steric hindrance from the ethyl groups can affect its basicity and ability to deprotonate a hydroxyl group.

Which of the following bases would favorably deprotonate a hydroxyl group?(d) Et3N